Fare Guide
Estimated lowest fares found within 7 days
Cheapest Airline
The cheapest airline(s) flying from San Jose to Chicago is Spirit Airlines.
Cheapest Month
April
Travel Period: April 2025 - March 2026
The cheapest month(s) to fly from San Jose to Chicago is April.
Cheapest Day of the Week
Friday
The cheapest day(s) of the week to fly from San Jose to Chicago is Friday.
How far is Chicago from San Jose?
The flight distance between San Jose and Chicago is 2958km. Check all available flights on Wego.
Popular Destinations From Chicago
Popular Destinations From San Jose
Popular Hotels in Chicago
- Clarion Inn Elmhurst - Oak Brook near I-88, I-290, I-294
- The Royal Sonesta Chicago Downtown
- Club Quarters Hotel Central Loop
- The Ritz-Carlton, Chicago
- Fairmont Chicago at Millennium Park Gold Experience
- Swissôtel Chicago
- Pendry Chicago
- Hotel Felix Chicago
- Hotel Saint Clair
- Best Western River North Hotel
